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The Secret Life of Whitey Bulger
  • June 26, 2014 : 13:06
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On a cool Wednesday evening, June 22, 2011, FBI agents with the Violent Crimes Task Force gathered at the Bureau’s Los Angeles headquarters on Wilshire Boulevard. They were joined by deputy U.S. marshals and heavily armed members of the LAPD SWAT team. The agents and cops were wired, tense with anticipation, for they were hoping to take down the FBI’s most wanted man, a criminal who had evaded capture for more than 16 years despite one of the largest worldwide manhunts in history.

That man, these agents believed, was living with his mistress in an apartment complex in Santa Monica just five miles from where the task force had assembled. James “Whitey” Bulger, criminal mastermind and Top Echelon FBI informant, was wanted for racketeering, extortion and drug dealing, as well as for his alleged participation in at least 19 murders. The agents believed Bulger, now 83 years old, was living under the alias Charles Gasko at 1012 Third Street, two blocks from the beach in Santa Monica, always paying his $1,145 rent on time, always in cash. The painstaking planning centered on how to capture Bulger now that the FBI was convinced it finally had him in its sights. Bulger was considered to be armed and extremely dangerous. An ex-con who had served time in California’s infamous Alcatraz penitentiary, he had sworn he would never go back to prison.

The Bureau did not want to screw it up this time. For years the agency had been humiliated time after time in locations around the world—from England to Australia, Italy to Ireland—as tips and reported sightings had failed to produce an arrest. Bulger was a phantom. There was rampant speculation that he was in fact the FBI’s least wanted fugitive, that the Bureau was merely making a show of trying to find him for fear of the consequences of his arrest—of what his secrets would reveal not just about the underworld but about the U.S. justice system itself.

At last the bust was about to go down. Sharpshooters had the tree-shaded building surrounded. Fearing a shootout, they decided not to break down the door and go in with guns blazing. Instead they concocted a ruse to lure the gangster from his lair. Agents contacted the building manager and instructed him to call the apartment. When the man they believed was Bulger answered, identifying himself as Mr. Gasko, the building manager told him a storage locker he was using in the basement of the building had been broken into and asked him to come down to make a claim.

The balding, white-haired man shuffled from the apartment and took the elevator to the basement. He wasn’t noticeably surprised or even upset when he walked into the trap and found a small army of federal agents with guns pointed at his head.

“James Bulger!” an agent yelled. “You’re under arrest! Put your hands on your head. Drop to your knees. Lie facedown. Hands behind your back.”

Agents swarmed around him like paparazzi on Brad Pitt. There was that familiar click and grip of the cuffs around his wrists.

“Yes,” he admitted, “I am James Bulger. You got me.”

Whitey Bulger smiled. At last he could stop running.

The agents took him back upstairs to the apartment, where his 60-year-old companion, Catherine Greig, awaited. There the investigators uncovered almost a million dollars in cash and a huge arsenal of weapons.

Bulger looked at his longtime live-in girlfriend, on the run with him for all these years. “Honey,” he said, “it’s time to go home.”

Phones rang in the offices of cops, agents, politicians, lawyers and prosecutors and in the homes and hideouts of crooks big and small all over the globe. Bulger’s flight had ended.

For Whitey Bulger was not just some run-of-the-mill bad guy. He was a mythic figure, a folk hero and ruthless murderer, the great criminal mastermind of our time. Loosely portrayed on the silver screen by Jack Nicholson in the Martin Scorsese film The Departed, Bulger ranks on a level with Gotti, Capone and Escobar, and even higher in his hometown of Boston. While executing his alleged 19 hits—strangling and stabbing his victims, dismembering their bodies and yanking out their teeth with pliers to thwart identification—Bulger and his partner, Stephen “the Rifleman” Flemmi, ruled the New England rackets for decades. All the while, it had long since been revealed, they were what is known as Top Echelon FBI criminal informants, or TEs. They were FBI assets. While Bulger and Flemmi ran New England’s underworld, they were protected and allowed to remain active by high-ranking officials within the Department of Justice.  

The FBI claims that after a 16-year manhunt it finally got wind of Bulger’s whereabouts after disseminating a 30-second public-service ad focused on his female companion, the elegant Greig, a former dental hygienist who was known to frequent beauty and nail salons. Aired primarily during women’s TV shows such as Ellen, The View and Dr. Oz, the ad produced more than 200 calls. According to inside sources, a young deputy U.S. marshal zeroed in on the lead that ultimately led agents to Bulger—a mere two days after the ads started to air.

The tip supposedly came from Miss Iceland 1974, Anna Björnsdóttir, still stunning at 58, a former B-movie star living in southern California. Björnsdóttir recognized Greig, whom she had befriended over a stray cat the ladies encountered in the streets of Santa Monica. That pussy cost Bulger his freedom and earned Björnsdóttir a $2 million reward.

But in the highest realms of the Department of Justice, and for students of the Bulger saga everywhere, the capture is not the end of the story but a new beginning. The gangster is a man of many secrets. He holds information that if exposed would send shock waves through the hallowed halls of the Department of Justice. Here is Bulger’s opportunity to end all the lies and tell the world what he knows.

There is one man who stands to gain the most by having the truth emerge. That man is former special agent John Connolly, Bulger’s FBI handler. A long time ago Connolly was a highly decorated agent. Now he has been in prison almost as long as Bulger was on the run. Connolly was headed to the yard for a workout at a federal prison in North Carolina when he heard about Bulger’s takedown. All through his workout, the news of the arrest played in Connolly’s mind. When he finished his exercises and returned to the housing unit for the evening count, Bulger’s capture was all over the airwaves.

Connolly’s side of perhaps the biggest law enforcement scandal of our time has never been fully told. Until now. In a series of telephone interviews from prison, Connolly spoke about the potentially game-changing arrest of Jim Bulger, his longtime Top Echelon criminal informant.

“Was I surprised to hear they caught Jim?” Connolly says. “Yes…but then again no. Yes because Jim had been a fugitive for so long, and as an FBI agent I realized the trail of someone that bright and that disciplined is usually ice-cold after 16 years. I knew Jim Bulger wasn’t going to be making the usual mistakes that result in fugitives being apprehended.

“Later,” Connolly remembered, “when I caught up with the news on TV, it hit me. This thing is going to get blown wide open. The potential evidentiary value of Whitey Bulger finally exposing the truth of his relationship with the Department of Justice—and what was done to me to cover that up—cannot be overestimated. That could finally set me free.”

South Boston is a neighborhood in the true sense of the word—an Irish American enclave physically and psychologically separate from the rest of the city. It even has its own song: “Southie Is My Hometown.” In the Old Harbor housing project, three Irish American youths were born before World War II to a shared destiny: One would reach the lofty heights of the famously clannish Massachusetts political machine, one would rise to the highest ranks of national law enforcement, while the third would seize the bloody crown of the New England underworld. All three would end up embroiled in a scandal that reached the highest levels of the American justice system.

Whitey Bulger got his elementary education in crime as a teenager running with a Southie street gang known as the Shamrocks. He became a journeyman criminal in league with a crew of bank robbers while still in his 20s and was named to the FBI’s most wanted list. Bulger did his first major prison stretch at the federal penitentiary in Atlanta. While there, in the 1950s, he volunteered to ingest massive doses of LSD as part of the CIA’s MK-Ultra program. Becoming a human guinea pig earned him a reduction in his sentence. He was transferred to Alcatraz, the Harvard of penitentiaries, where he received the equivalent of a doctorate in criminality. An avid reader and a long-range thinker, Bulger studied military history and warfare tactics while locked up, absorbing such classics as Sun Tzu’s The Art of War and Machiavelli’s The Prince. He emerged from the penitentiary a master criminal on acid and was soon in the thick of the mob wars raging in Boston in the 1960s and 1970s, working his way up until he was running the notorious Winter Hill gang out of Southie.

Whitey’s younger brother Billy took the opposite road. He became a “triple eagle” graduate of Boston College High School, Boston College and Boston College Law School before entering local politics. After 17 years in the state senate, Billy was named president of the University of Massachusetts. Later, after his gangster brother absconded from the law in 1995, Billy was hounded out of public life by then Massachusetts governor Mitt Romney for refusing to testify before a grand jury investigating Whitey.

Like most of the kids in the neighborhood, young Johnny Connolly was in awe of Whitey. He heard the stories of Whitey having an affair with a stripper from the Old Howard burlesque hall and running off with a traveling circus while most kids were still in school. But Connolly was closer in age to Billy Bulger, and they became friends. Connolly chose to follow Billy’s lead. He got a good education before embarking on a career in law enforcement with the FBI.

As a young street agent in Manhattan, Connolly was walking along Third Avenue on a cold December day in 1972 when he recognized fugitive Boston mafioso Francis “Cadillac Frank” Salemme walking toward him. Salemme was a suspect in numerous gangland hits and had been indicted for planting a car bomb that blew one of the legs off a Boston attorney. After a foot chase that ended when Connolly tackled Salemme at the corner of 81st Street, Connolly took the fugitive into custody virtually single-handedly. With the Salemme arrest, Connolly got his wish: He was transferred back to his hometown to work the underbelly of Boston, where both the Irish and Italian mobs were thriving even as they warred for dominance.

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read more: entertainment, News, issue december 2012


  • Anonymous
    John should not only be exonerated by whitey Bulger but also by the entire justice departments !! Great article
  • Anonymous
    I enjoyed the article but as a friend of "a young US Marshall zeroed in on the lead" I find it odd that Playboy didn't mention his name. Neil Sullivan was THE reason that Whitey Bulger was captured. The FBI was secondary to Neils' relentless work to apprehend a fugitive and his work should be noted.